1-(5-(p-methoxyphenyl)furfurylidene)amino)hydantoin

ABSTRACT

The title compound is a useful muscle relaxant.

United States Patent [191 [1 1 3,843,636 White, Jr. Oct. 22, 1974 l-(s-(P-METHOXYPHENYLWUR- FURYLIDENEDAMINO) HYDANTOIN [75] Inventor: Ralph L. White, Jr., Norwich, NY. [73] Assignee: Morton-Norwich Products, Inc., Norwich, NY,

[22] Filed: Jan. 25, 1974 [2]] Appl. No.: 436,466

[52] US. Cl. 260/240 G, 424/274 [5 1] Int. Cl C09b 23/00 [58] Field of Search 260/240 A, 240 G [56] References Cited UNITED STATES PATENTS 3,415,821 12/1968 Davis et all. 260/240 G OTHER PUBLICATIONS Synder et al., J. Med. Chem. Vol. 10, pages 807 to 810, (1967). 58, pages 1,528 to 1,537, 1

Burger, Medicinal Chemistry, Part ll, Third Ed., Chapter 58, pages 1,528 to 1,537, Wiley-lnterscience, NY. (1970).

Primary Examiner-John D. Randolph Attorney, Agent, or FirmAnthonyJ. Franze [57 ABSTRACT The title compound is a useful muscle relaxant.

1 Claim, No Drawings l-(5-(P-METHOXYPHENYIJFUR- FURYLIDENE)AMINO) HYDANTOIN This invention is concerned with the chemical compound v l-{ 5.-(p-methoxyphenyl )furfurylidenelamino} hydantoin. sesses pharmacological activity. In particular it exhibits skeletal muscle relaxant activity when administered perorally or intravenously to warm-blooded animals. Thus when administered intravenously in a pharmaceutically acceptable solvent, such as aqueous sodium hydroxide-mannitol solution, at a dose of about 1-00 mg./kg. to rats, inhibition of the twitch response of the gastrocnemius muscle is elicited.

This compound is preferably prepared in accordance with the following example:

A mixture of 62 g (0.50 mole) of p-anisidine in 50 ml of water and I35 ml of concentrated hydrochloric acid was diazotized by dropwise addition of 36 g (0.52 mole) of sodium nitrite in 100 ml of water, with the pot temperature kept below Thirty minutes after completing the addition, the solution was filtered and added to 61.5 g (0.64 mole) of furfural in 200 ml ofwater, followed by addition of 23 g of cupric chloride dihydrate This compound pos in l00 ml of water. The stirred mixture was heated at 5060 for four hours then stirred overnight without heating. The solution was extracted with two 500 ml in 150 ml of water. After 2 hours the solid was col lected, washed with 100 ml of ethanol and recrystallized by suspending the solid in 500 ml of dioxane and adding ml of dimethylformamide. After 5 days 1 1.75 g of product was collected (8%), mp. 266-269.

Anal. Calcd. for C H N O C, 60.20; H, 4.38; N,

Found: C, 60.01; H, 4.35; N, 14.09. What is claimed is: V v V 1. 1-{[5-(p-Methoxyphenyllfutfurylidene]amino} hydantoin. 

1. 1-(5-(P-METHOXYPHENYL)FURFURYLIDENE)AMINO) HYDANTOIN. 